US11812659B2 - Organic electroluminescence device and polycyclic compound for organic electroluminescence device - Google Patents

Organic electroluminescence device and polycyclic compound for organic electroluminescence device Download PDF

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US11812659B2
US11812659B2 US17/028,922 US202017028922A US11812659B2 US 11812659 B2 US11812659 B2 US 11812659B2 US 202017028922 A US202017028922 A US 202017028922A US 11812659 B2 US11812659 B2 US 11812659B2
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Seulong KIM
Eu-Gene Oh
Munsoo KIM
Juwan Maeng
Kap-jong HAN
Jaeweon Hur
Hyewon CHOI
KyungSik KIM
Sung-Soo Bae
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Samsung Display Co Ltd
Lapto Co Ltd
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Definitions

  • One or more aspects of embodiments of the present disclosure relate to an organic electroluminescence device and a polycyclic compound used therein, and for example, to a polycyclic compound used as a light-emitting material and an organic electroluminescence device including the same.
  • An organic electroluminescence display differs from a liquid crystal display by being a so-called self-luminescent display, in which holes and electrons injected from a first electrode and a second electrode recombine in an emission layer, and a light-emitting material that includes an organic compound in the emission layer emits light to achieve display.
  • an organic electroluminescence device In the application of an organic electroluminescence device to a display, a decrease in driving voltage and an increase of emission efficiency and/or lifespan of the organic electroluminescence device are beneficial, and development of materials for an organic electroluminescence device capable of stably accomplishing these characteristics is desired.
  • TTA triplet-triplet annihilation
  • One or more aspects of embodiments of the present disclosure are directed toward an organic electroluminescence device having improved emission efficiency.
  • One or more aspects of embodiments of the present disclosure are directed toward a polycyclic compound that may improve the emission efficiency of an organic electroluminescence device.
  • One or more example embodiments of the present disclosure provide an organic electroluminescence device including a first electrode, a second electrode oppositely disposed to the first electrode, and an emission layer disposed between the first electrode and the second electrode and including a polycyclic compound represented by Formula 1:
  • L may be a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring
  • A may be a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, where at least one among L and A includes an electron acceptor substituent, n may be an integer of 1 to 3, and D may be represented by Formula 2:
  • X may be O, S, NR 1 , or SiR 2 R 3
  • Y 1 to Y 11 may each independently be N or CR 4
  • R 1 to R 4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or may be combined with an adjacent group to form a ring, and any one among R 1 to R 4 may be a connecting part with (e.g., connected with) L in Formula 1.
  • the emission layer may be to emit delayed fluorescence.
  • the emission layer may be a delayed fluorescence emission layer including a host and a dopant.
  • the dopant may include the polycyclic compound represented by Formula 1.
  • the emission layer may include a host having a first lowest triplet excitation energy level, a first dopant having a second lowest triplet excitation energy level lower than the first lowest triplet excitation energy level, and a second dopant having a third lowest triplet excitation energy level lower than the second lowest triplet excitation energy level.
  • the first dopant may include the polycyclic compound represented by Formula 1.
  • the first dopant may be a delayed fluorescence dopant
  • the second dopant may be a fluorescence dopant
  • the organic electroluminescence device may further include a hole transport region disposed between the first electrode and the emission layer; and an electron transport region disposed between the emission layer and the second electrode.
  • A may be represented by one of Formula A-1 to Formula A-3:
  • W 1 to W 12 may each independently be N or CR 13 , Z 1 may be O or S, Z 2 may be O, S, NR 14 , CR 15 R 16 , or SiR 17 R 18 , m may be 0 or 1, R 5 to R 18 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or may be combined with an adjacent group to form a ring, at least one among R 7 to R 12 may be a hal
  • A may be represented by one of Formula A-1-1 to Formula A-3-3:
  • W 1 to W 12 , Z 1 , Z 2 , m, and R 5 to R 18 may each independently be the same as defined in Formula A-1 to Formula A-3.
  • the polycyclic compound represented by Formula 1 may be represented by Formula 3: D 1 -L 1 -A-L 2 D 2 Formula 3
  • L 1 and L 2 may each independently be a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, D 1 may be represented by Formula 2, and D 2 may be an electron donor substituent.
  • A may be the same as defined in Formula 1.
  • D 2 may be a substituted or unsubstituted arylamine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • D may be represented by one of Formula 2-1 to Formula 2-5:
  • Y 1 to Y 11 , and R 1 to R 4 may each independently be the same as defined in Formula 2.
  • L may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzoxazolylene group, a substituted or unsubstituted benzothiazolylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted oxazolopyridinylene group, a substituted or unsubstituted thiazolopyridinylene group, a substituted or unsubstituted dibenzoborynylene group, or a substituted or unsubstituted dibenzoxaborynylene group.
  • One or more example embodiments of the present disclosure provide a polycyclic compound represented by Formula 1 above.
  • the first electrode and the second electrode may each independently include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and an oxides of one or more thereof.
  • an absolute value of a difference between a lowest singlet excitation energy level (S1) and a lowest triplet excitation energy level (T1) in the polycyclic compound represented by Formula 1 may be about 0.2 eV.
  • FIG. 1 is a schematic cross-sectional view illustrating an organic electroluminescence device according to an embodiment of the present disclosure
  • FIG. 2 is a schematic cross-sectional view illustrating an organic electroluminescence device according to an embodiment of the present disclosure
  • FIG. 3 is a schematic cross-sectional view illustrating an organic electroluminescence device according to an embodiment of the present disclosure.
  • FIG. 4 is a schematic cross-sectional view illustrating an organic electroluminescence device according to an embodiment of the present disclosure.
  • FIGS. 1 to 4 are schematic cross-sectional views showing organic electroluminescence devices according to example embodiments of the present disclosure.
  • a first electrode EL 1 and a second electrode EL 2 are oppositely disposed, and between the first electrode EL 1 and the second electrode EL 2 , a plurality of organic layers may be disposed.
  • the plurality of the organic layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR.
  • the organic electroluminescence device 10 of an embodiment may include a first electrode EL 1 , a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode, stacked in order.
  • a capping layer CPL may be further disposed on the second electrode EL 2 .
  • the organic electroluminescence device 10 of an embodiment may include a polycyclic compound of an embodiment, which will be explained later, in at least one organic layer selected from the plurality of organic layers disposed between the first electrode EL 1 and the second electrode EL 2 .
  • the organic electroluminescence device 10 of an embodiment may include a polycyclic compound of an embodiment in the emission layer EML disposed between the first electrode EL 1 and the second electrode EL 2 .
  • an embodiment of the present disclosure is not limited thereto.
  • the organic electroluminescence device 10 of an embodiment may include a polycyclic compound of an embodiment in at least one organic layer included in the hole transport region HTR and the electron transport region ETR, which are among the plurality of organic layers disposed between the first electrode EL 1 and the second electrode EL 2 in addition to the emission layer EML, or for example, may include a polycyclic compound of an embodiment in a capping layer CPL disposed on the second electrode EL 2 .
  • FIG. 2 shows the cross-sectional view of an organic electroluminescence device 10 of an embodiment in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL.
  • FIG. 3 shows the cross-sectional view of an organic electroluminescence device 10 of an embodiment, wherein the hole transport region HTR includes the hole injection layer HIL, the hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes the electron injection layer EIL, the electron transport layer ETL, and a hole blocking layer HBL.
  • FIG. 4 shows the cross-sectional view of an organic electroluminescence device 10 of an embodiment further including a capping layer CPL disposed on the second electrode EL 2 .
  • the emission layer EML is described as including the polycyclic compound of an embodiment but embodiments of the present disclosure are not limited thereto.
  • the polycyclic compound according to an embodiment may be included in the hole transport region HTR, the electron transport region ETR, and/or the capping layer CPL.
  • the first electrode EL 1 may have conductivity (e.g., may be conductive).
  • the first electrode EL 1 may be formed using a metal alloy and/or a conductive compound.
  • the first electrode EL 1 may be an anode.
  • the first electrode EL 1 may be a pixel electrode.
  • the first electrode EL 1 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
  • the first electrode EL 1 may include or be formed of a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.
  • the first electrode EU may include or be formed of silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF/Ca, LiF/Al, molybdenum (Mo), titanium (Ti), a compound thereof, or a mixture thereof (for example, a mixture of Ag and Mg).
  • the first electrode EU may have a structure including a plurality of layers including a reflective layer and/or a transflective layer formed using the above materials, and a transmissive conductive layer formed using ITO, IZO, ZnO, ITZO, etc.
  • the first electrode EL 1 may include a three-layer structure of ITO/Ag/ITO.
  • the thickness of the first electrode EU may be about 1,000 ⁇ to about 10,000 ⁇ , for example, about 1,000 ⁇ to about 3,000 ⁇ .
  • the hole transport region HTR is disposed on the first electrode EL 1 .
  • the hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, or an electron blocking layer EBL.
  • the thickness of the hole transport region HTR may be, for example, about 50 ⁇ to about 1,500 ⁇ .
  • the hole transport region HTR may have or be a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure including a plurality of layers formed using a plurality of different materials.
  • the hole transport region HTR may have a single layer structure including the hole injection layer HIL or the hole transport layer HTL, or a single layer structure formed using a hole injection material and a hole transport material (e.g., mixed together).
  • the hole transport region HTR may have a structure of a single layer formed using a plurality of different materials, or a multi-layer structure stacked from (on) the first electrode EL 1 and including a hole injection layer HIL/hole transport layer HTL, hole injection layer HIL/hole transport layer HTL/hole buffer layer, hole injection layer HIL/hole buffer layer, hole transport layer HTL/hole buffer layer, or hole injection layer HIL/hole transport layer HTL/electron blocking layer EBL, without limitation.
  • the hole transport region HTR may be formed using any suitable method (such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method).
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
  • LB Langmuir-Blodgett
  • LITI laser induced thermal imaging
  • the hole injection layer HIL may include, for example, a phthalocyanine compound (such as copper phthalocyanine), N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine (DNTPD), 4,4′,4′′-tris(3-methylphenylphenylamino) triphenylamine (m-MTDATA), 4,4′,4′′-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4′′-tris ⁇ N,-2-naphthyl)-N-phenylamino ⁇ -triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/dodecylbenzenesulfonic acid (PANI/DB
  • the hole transport layer HTL may include, for example, carbazole derivatives (such as N-phenyl carbazole and/or polyvinyl carbazole), fluorene-based derivatives, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), triphenylamine-based derivatives (such as 4,4′,4′′-tris(carbazol-9-yl)triphenylamine (TCTA)), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzeneamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 1,3-bis(N-car
  • the thickness of the hole transport region HTR may be about 100 ⁇ to about 10,000 ⁇ , for example, about 100 ⁇ to about 5,000 ⁇ .
  • the thickness of the hole injection region HIL may be, for example, about 30 ⁇ to about 1,000 ⁇ , and the thickness of the hole transport layer HTL may be about 30 ⁇ to about 1,000 ⁇ .
  • the thickness of the electron blocking layer EBL may be about 10 ⁇ to about 1,000 ⁇ .
  • the hole transport region HTR may further include a charge generating material to increase conductivity in addition to the above-described materials.
  • the charge generating material may be dispersed substantially uniformly or non-uniformly in the hole transport region HTR.
  • the charge generating material may be, for example, a p-dopant.
  • the p-dopant may be a quinone derivative, metal oxide, or cyano group-containing compound, without limitation.
  • Non-limiting examples of the p-dopant include quinone derivatives (such as tetracyanoquinodimethane (TCNQ) and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide and/or molybdenum oxide), etc.
  • quinone derivatives such as tetracyanoquinodimethane (TCNQ) and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)
  • metal oxides such as tungsten oxide and/or molybdenum oxide
  • the hole transport region HTR may further include at least one of a hole buffer layer or an electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL.
  • the hole buffer layer may compensate for an optical resonance distance according to the wavelength of light emitted from the emission layer EML to thereby increase the light emission efficiency.
  • the materials included in the hole transport region HTR may be the same as the materials included in the hole buffer layer.
  • the electron blocking layer EBL may prevent or reduce electron injection from the electron transport region ETR into the hole transport region HTR.
  • the emission layer EML is disposed on the hole transport region HTR.
  • the emission layer EML may have a thickness of, for example, about 100 ⁇ to about 1,000 ⁇ , or about 100 ⁇ to about 300 ⁇ .
  • the emission layer EML may have or be a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.
  • the emission layer EML may include the polycyclic compound of an embodiment.
  • substituted or unsubstituted refers to being unsubstituted, or being substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boryl group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group.
  • each of the substituents may be further substituted or unsubstituted.
  • a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with
  • the term “forming a ring via combination with an adjacent group” may refer to forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle when the group or atom is bonded to an adjacent group.
  • hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.
  • heterocycle includes an aliphatic heterocycle and an aromatic heterocycle.
  • the hydrocarbon ring and the heterocycle, and in some embodiments the ring formed via combination with an adjacent group may be a monocyclic ring or a polycyclic ring. In some embodiments, the ring formed via combination with an adjacent group may be further combined with another ring to form a spiro structure.
  • adjacent group may refer to a substituent on the same atom or point, a substituent on an atom that is directly connected to the base atom or point, or a substituent sterically positioned (e.g., within intramolecular bonding distance) to the corresponding substituent.
  • the two methyl groups may be interpreted as “adjacent groups” to each other
  • 1,1-diethylcyclopentane the two ethyl groups may be interpreted as “adjacent groups” to each other.
  • halogen atom may refer to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • alkyl may refer to a linear, branched or cyclic alkyl group.
  • the carbon number of the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6.
  • Non-limiting examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl
  • hydrocarbon ring may refer to an optional functional group or substituent derived from an aliphatic hydrocarbon ring, or an optional functional group or substituent derived from an aromatic hydrocarbon ring.
  • the carbon number of the hydrocarbon ring for forming a ring may be 5 to 60.
  • heterocyclic group may refer to an optional functional group of substituent derived from a heterocycle including at least one heteroatom as a ring-forming element.
  • the carbon number of the heterocyclic group for forming a ring may be 5 to 60.
  • aryl group may refer to an optional functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the carbon number for forming a ring in the aryl group may be 6 to 30, 6 to 20, or 6 to 15.
  • Non-limiting examples of the aryl group include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinqphenyl, sexiphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, chrysenyl, etc.
  • the fluorenyl group may be substituted (e.g., at the 9H position), and two substituents at the 9H position may be combined with each other to form a spiro structure.
  • a substituted fluorenyl group are as follows. However, an embodiment of the present disclosure is not limited thereto.
  • heteroaryl may refer to an aryl group including one or more boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S) atoms.
  • B boron
  • O oxygen
  • N nitrogen
  • P phosphorus
  • Si silicon
  • S sulfur
  • the heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl.
  • the carbon number for forming a ring of the heteroaryl may be 2 to 30, 2 to 20, or 2 to 10.
  • heteroaryl examples include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridyl, pyridazine, pyrazinyl, quinoline, quinazoline, quinoxaline, phenoxazine, phthalazine, pyrido pyrimidine, pyrido pyrazine, pyrazino pyrazine, isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene, benzofuran,
  • sil group includes an alkylsilyl group and an arylsilyl group.
  • Non-limiting examples of the silyl group include trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.
  • an embodiment of the present disclosure is not limited thereto.
  • boryl group includes an alkyl boryl group and an aryl boryl group.
  • Non-limiting examples of the boryl group include a trimethylboryl group, a triethylboryl group, a t-butyldimethylboryl group, a triphenylboryl group, a diphenylboryl group, a phenylboryl group, etc.
  • the carbon number of the amine group is not specifically limited, but may be 1 to 30.
  • the amine group may include an alkyl amine group and an aryl amine group.
  • Non-limiting examples of the amine group include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, a triphenylamine group, etc.
  • heterocyclic group may include one or more of B, O, N, P, Si and S as heteroatoms.
  • the heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and in some embodiments may include a heteroaryl group.
  • the carbon number for forming a ring of the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.
  • the polycyclic compound of an embodiment may include a substituted or unsubstituted indolophenazine group, or a substituted or unsubstituted indolophenoxazine group.
  • the polycyclic compound of an embodiment may include a substituted or unsubstituted indolophenazine group or a substituted or unsubstituted indolophenoxazine group as an electron donor substituent.
  • the polycyclic compound of an embodiment may be represented by Formula 1:
  • L may be a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring.
  • L may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzoxazolylene group, a substituted or unsubstituted benzothiazolylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted oxazolopyridinylene group, a substituted or unsubstituted thiazolopyridinylene group, a substituted or unsubstituted dibenzoborynylene group, or a substituted or unsubstituted dibenzoxaborynylene group.
  • n may be an integer of 1 to 3.
  • A may be a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
  • A may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted imidazopyridine group, a substituted or unsubstituted oxazolopyridine group, a substituted or unsubstituted thiazolopyridine group, a substituted or unsubstituted dibenzoborynylene group, or a substituted or unsubstituted dibenzoxaborynyl group.
  • A may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • L and A may include an electron acceptor substituent.
  • L may be a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, and A may include an electron acceptor substituent.
  • L may include an electron acceptor substituent, and A may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • D is an electron donor substituent.
  • D may be represented by Formula 2:
  • X may be O, S, NR 1 , or SiR 2 R 3 . In an embodiment, X may be O or NR 1 .
  • the polycyclic compound represented by Formula 1 may include an indolophenoxazine group as an electron donor substituent.
  • X is NR 1
  • the polycyclic compound represented by Formula 1 may include an indolophenazine group as an electron donor substituent.
  • Y 1 to Y 11 may each independently be N or CR 4 . In an embodiment, each (all) of Y 1 to Y 11 may be CR 4 . In an embodiment, any one of Y 1 to Y 11 may be N and the rest (remainder) may be CR 4 .
  • R 1 to R 4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
  • R 1 to R 4 may each independently be combined with an adjacent group to form a ring.
  • R 1 may be a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.
  • R 4 may be a hydrogen atom. When a plurality of R 4 are present, the R 4 groups may be the same or different.
  • one of R 1 to R 4 may represent a connection with (to) L in Formula 1.
  • X may be NR 1
  • R 1 may represent a connection with L.
  • Y 2 or Y 10 may be CR 4
  • R 4 may represent a connection with L in Formula 1.
  • a or the electron accepting substituent on L may be represented by one of Formula A-1 to Formula A-3:
  • W 1 to W 12 may each independently be N or CR 13 .
  • W 1 to W 4 may each (all) be CR 13 .
  • W 1 may be N, and W 2 to W 4 may be CR 13 .
  • W 5 to W 12 may each (all) be CR 13 .
  • Z 1 may be O or S.
  • the substituent represented by Formula A-1 may be a benzoxazole moiety.
  • the substituent represented by Formula A-1 may be a benzothiazole moiety.
  • Z 2 may be O, S, NR 14 , CR 15 R 16 , or SiR 17 R 18 . In an embodiment, Z 2 may be O, or CR 15 R 16 . When Z 2 is O, the substituent represented by Formula A-2 may be a dibenzoxaborynyl moiety. When Z 2 is CR 15 R 16 , the substituent represented by Formula A-2 may be a dibenzoborynyl moiety.
  • m may be 0 or 1.
  • Z 2 is not present (included) in the substituent represented by Formula A-2, and two six-member aromatic rings are substituted on a boron atom (e.g., without being bonded at another point).
  • the substituent represented by Formula A-2 may be a diphenylborane moiety.
  • R 5 to R 18 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring.
  • R 5 and R 6 may each (all) be hydrogen atoms.
  • At least one selected from R 7 to R 12 may be a halogen atom or a cyano group. In an embodiment, one or two selected from R 7 to R 12 may be cyano groups. In some embodiments, R 7 to R 12 may each (all) be halogen atoms. In some embodiments, R 7 to R 12 may each (all) be fluorine atoms.
  • A may be represented by one of Formula A-1-1 to Formula A-3-3:
  • W 1 to W 12 , Z 1 , Z 2 , m, and R 5 to R 18 may be the same as described herein in connection with Formula A-1 to Formula A-3.
  • D may be represented by one of Formula 2-1 to Formula 2-5:
  • Y 1 to Y 11 , and R 1 to R 4 may be the same as described herein in connection with Formula 2.
  • the polycyclic compound represented by Formula 1 may be represented by Formula 3: D 1 -L 1 -A-L 2 -D 2 Formula 3
  • L 1 and L 2 may each independently be a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring.
  • L 1 and L 2 may each independently be a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzoxazolylene group, a substituted or unsubstituted benzothiazolylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted oxazolopyridinylene group, a substituted or unsubstituted thiazolopyridinylene group, a substituted or unsubstituted dibenzoborynylene group, or a substituted or unsubstituted dibenzoxaborynylene group.
  • L 1 and L 2 may be the same as described herein in connection with L
  • D 1 may be an electron donor substituent.
  • D 1 may be represented by Formula 2.
  • D 1 may be the same as described herein in connection with D in Formula 1.
  • D 2 may be an electron donor substituent.
  • D 2 may be a substituted or unsubstituted arylamine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • D 1 and D 2 may be different from each other.
  • D 1 may be a substituted or unsubstituted indolophenazine group
  • D 2 may be a substituted or unsubstituted arylamine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • D 1 may be a substituted or unsubstituted indolophenoxazine group
  • D 2 may be a substituted or unsubstituted arylamine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted acridine group, or a substituted or unsubstituted phenoxazine group.
  • the polycyclic compound of an embodiment may be selected from the compounds represented in Compound Group 1 and Compound Group 2.
  • the organic electroluminescence device 10 of an embodiment may include at least one polycyclic compound selected from Compound Group 1 in the emission layer EML.
  • the polycyclic compound represented by Formula 1 may be a material to emit thermally activated delayed fluorescence.
  • the polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescence (TADF) dopant having a triple-singlet energy difference ( ⁇ E ST ) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level) of about 0.2 eV or less.
  • TADF thermally activated delayed fluorescence
  • ⁇ E ST triple-singlet energy difference
  • the ⁇ E ST of the polycyclic compound represented by Formula 1 may be about 0.10 eV or less.
  • the emission layer EML may be to emit delayed fluorescence.
  • the emission layer EML may be to emit thermally activated delayed fluorescence (TADF).
  • TADF thermally activated delayed fluorescence
  • the compound of an embodiment represented by Formula 1 may be a donor (D)-acceptor (A) type (e.g., structure) delayed fluorescence dopant material having a donor and an acceptor bonded within the same compound.
  • D donor
  • A acceptor
  • an indolophenazine or indolophenoxazine moiety may correspond to an electron donor
  • a substituent represented by “A” may correspond to an electron acceptor.
  • the compound of an embodiment represented by Formula 1 may be a D-A type (structure) thermally activated delayed fluorescence dopant.
  • the compound of an embodiment represented by Formula 1 may be further represented by Formula 3 and may be a D(donor)-A(acceptor)D-(donor) type delayed fluorescence dopant material.
  • the substituent parts represented by D 1 and D 2 may correspond to electron donors, and the substituent part represented by “A” may correspond to an electron acceptor.
  • the emission layer EML of the organic electroluminescence device 10 may be to emit red light or green light. However, an embodiment of the present disclosure is not limited thereto, and in some embodiments the emission layer EML may be to emit blue light.
  • the compound of an embodiment has a novel compound structure including an indolophenazine or indolophenoxazine moiety as an electron donor and may be a material to emit thermally activated delayed fluorescence, and may be used as a material in an emission layer of an organic electroluminescence device to improve emission efficiency.
  • the compound according to an embodiment is used as a light-emitting material to emit light in a green or red wavelength region, and may show excellent emission efficiency.
  • the organic electroluminescence device 10 of an embodiment may include a plurality of emission layers.
  • the plurality of emission layers may be stacked in order in the device, and for example, the organic electroluminescence device 10 including the plurality of emission layers may be to emit white light.
  • the organic electroluminescence device including the plurality of emission layers may be an organic electroluminescence device having a tandem structure.
  • at least one emission layer EML may include the above-described polycyclic compound of an embodiment.
  • the emission layer EML may include a host in combination with the above-described polycyclic compound as the dopant.
  • the emission layer EML may include a host to emit delayed fluorescence and a dopant to emit delayed fluorescence, and may include the above-described polycyclic compound as the dopant to emit delayed fluorescence.
  • the emission layer EML may include the polycyclic compound represented in the above-described Compound Group 1 as a thermally activated delayed fluorescence dopant.
  • the emission layer EML is a delayed fluorescence emission layer
  • the emission layer EML may include any suitable host material and the above-described polycyclic compound.
  • the polycyclic compound may be used as a TADF dopant.
  • any suitable material may be used and may be selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, chrysene derivatives, etc., without specific limitation.
  • pyrene derivatives, perylene derivatives, and anthracene derivatives may be used.
  • an anthracene derivative represented by Formula 4 may be used as the host material in the emission layer EML.
  • R 31 to R 40 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, or may be combined with an adjacent group to form a ring. In some embodiments, R 31 to R 40 may be combined with an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.
  • c and d may each independently be an integer of 0 to 5.
  • Formula 4 may be represented by one selected from Formula 3-1 to Formula 3-16:
  • the emission layer EML may include as a host material, tris(8-hydroxyquinolino)aluminum (Alq3), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4′,4′′-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2,4′
  • an embodiment of the present disclosure is not limited thereto, and in some embodiments, the compound of an embodiment may be used as the host material of the emission layer EML.
  • any suitable dopant material may be used in addition to the compound of an embodiment in the emission layer EML.
  • the emission layer EML may further include any suitable dopant material.
  • the emission layer EML may include as a dopant, styryl derivatives (for example, 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi)), perylene and derivatives thereof (for example, 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and derivatives thereof (for example, 1,1-dipyrene, 1,4
  • the emission layer EML may include two dopant materials having different lowest triplet excitation energy levels (T1 levels) from each other.
  • the emission layer EML may include a host having a first lowest triplet excitation energy level, a first dopant having a second lowest triplet excitation energy level that is lower than the first lowest triplet excitation energy level, and a second dopant having a third lowest triplet excitation energy level that is lower than the second lowest triplet excitation energy level.
  • the emission layer EML may include the above-described polycyclic compound as the first dopant.
  • the first dopant may be a delayed fluorescence dopant
  • the second dopant may be a fluorescence (e.g., fluorescent) dopant.
  • the polycyclic compound represented by Formula 1 may play the role of an assistant dopant.
  • the emission layer EML of the organic electroluminescence device 10 of an embodiment includes a plurality of dopants
  • the emission layer EML may include the polycyclic compound of an embodiment as the first dopant and any suitable dopant material (examples of which are described above) as the second dopant.
  • the emission layer EML may further include, as the second dopant, one selected from the group consisting of spiro-DPVBi, spiro-6P, distyryl-benzene (DSB), distyryl-arylene (DSA), a polyfluorene (PFO)-based polymer, and a poly(p-phenylene vinylene) (PPV)-based polymer.
  • the second dopant may be a metal complex or an organometallic complex (such as (4,6-F 2 ppy) 2 Irpic, perylene the derivatives thereof, etc.).
  • the emission layer EML may be to emit green light or red light
  • the second dopant material may be any suitable dopant as described above, any suitable green fluorescence dopant, or any suitable red fluorescence dopant.
  • the emission layer EML may be a phosphorescence (e.g., phosphorescent) emission layer.
  • the polycyclic compound according to an embodiment may be included in the emission layer EML as a phosphorescence host material.
  • the electron transport region ETR is provided on the emission layer EML.
  • the electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, or an electron injection layer EIL.
  • a hole blocking layer HBL hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the electron transport region ETR may have or be a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.
  • the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or a single layer structure formed using an electron injection material and an electron transport material (e.g., together).
  • the electron transport region ETR may have a single layer structure formed using a plurality of different materials, or a structure stacked from the emission layer EML of electron transport layer ETL/electron injection layer EIL, or hole blocking layer HBL/electron transport layer ETL/electron injection layer EIL, without limitation.
  • the thickness of the electron transport region ETR may be, for example, about 100 ⁇ to about 1,500 ⁇ .
  • the electron transport region ETR may be formed using any suitable method (such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method).
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
  • LB Langmuir-Blodgett
  • LITI laser induced thermal imaging
  • the electron transport region ETR may include an anthracene-based compound.
  • the electron transport region ETR may include, for example, tris(8-hydroxyquinolinato)aluminum (Alq3), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1
  • the thickness of the electron transport layer ETL may be about 100 ⁇ to about 1,000 ⁇ and may be, for example, about 150 ⁇ to about 500 ⁇ . When the thickness of the electron transport layer ETL satisfies the above-described range, satisfactory electron transport properties may be obtained without a substantial increase in driving voltage.
  • the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl, RbI, and/or CuI), a lanthanide metal (such as ytterbium (Yb), a metal oxide (such as Li 2 O and/or BaO), and/or lithium quinolate (LiQ).
  • a metal halide such as LiF, NaCl, CsF, RbCl, RbI, and/or CuI
  • a lanthanide metal such as ytterbium (Yb)
  • a metal oxide such as Li 2 O and/or BaO
  • LiQ lithium quinolate
  • the electron injection layer EIL may be formed using a mixture of an electron transport material and an insulating organo metal salt.
  • the organo metal salt may be a material having an energy band gap of about 4 eV or more.
  • the organo metal salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and/or metal stearates.
  • the thickness of the electron injection layer EIL may be about 1 ⁇ to about 500 ⁇ , or about 3 ⁇ to about 300 ⁇ . When the thickness of the electron injection layer EIL satisfies the above described range, satisfactory electron injection properties may be obtained without inducing substantial increase of a driving voltage.
  • the electron transport region ETR may include a hole blocking layer HBL as described above.
  • the hole blocking layer HBL may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), or 4,7-diphenyl-1,10-phenanthroline (Bphen).
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • Bphen 4,7-diphenyl-1,10-phenanthroline
  • an embodiment of the present disclosure is not limited thereto.
  • the second electrode EL 2 is provided on the electron transport region ETR.
  • the second electrode EL 2 may be a common electrode or a cathode.
  • the second electrode EL 2 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
  • the second electrode EL 2 may be formed using a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, etc.
  • the second electrode EL 2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, a compound thereof, and/or a mixture thereof (for example, a mixture of Ag and Mg).
  • the second electrode EL 2 may have a multilayered structure including a reflective layer and/or a transflective layer formed using the above-described materials, and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.
  • the second electrode EL 2 may be connected with an auxiliary electrode.
  • the resistance of the second electrode EL 2 may decrease.
  • a capping layer CPL may be further disposed on the second electrode EL 2 of the organic electroluminescence device 10 of an embodiment.
  • the capping layer CPL may include, for example, ⁇ -NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4′,N4′-tetra(biphenyl-4-yl) biphenyl-4,4′-diamine (TPD15), 4,4′,4′′-tris(carbazol-9-yl)triphenylamine (TCTA), etc.
  • the organic electroluminescence device 10 includes the polycyclic compound of an embodiment in the emission layer EML between the first electrode EL 1 and the second electrode EL 2 , and may thereby exhibit high emission efficiency properties.
  • the polycyclic compound according to an embodiment may be a thermally activated delayed fluorescence dopant
  • the emission layer EML may include the polycyclic compound of an embodiment to emit thermally activated delayed fluorescence. Accordingly, high emission efficiency properties may be achieved.
  • the polycyclic compound of an embodiment may be included in an organic layer other than the emission layer EML as a material for the organic electroluminescence device 10 .
  • the organic electroluminescence device 10 may include the polycyclic compound in at least one organic layer disposed between the first electrode EL 1 and the second electrode EL 2 , and/or in the capping layer CPL disposed on the second electrode EL 2 .
  • the polycyclic compound of an embodiment may have a smaller energy difference ( ⁇ E ST ) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level) through a novel structure including an indolophenazine or indolophenoxazine moiety when compared with compounds in the related art. Accordingly, when the polycyclic compound of an embodiment is used as a material for an organic electroluminescence device, the efficiency of the organic electroluminescence device may be further improved.
  • the synthetic method of the polycyclic compounds according to example embodiments will be explained by referring to synthetic methods for Compound 4, Compound 5, Compound 6, Compound 10, Compound 11, Compound 38, Compound 72, and Compound 77.
  • the synthetic methods of the polycyclic compounds explained below are only embodiments, and synthetic methods of the polycyclic compound according to an embodiment of the present disclosure are not limited thereto.
  • Polycyclic Compound 4 according to an embodiment may be synthesized, for example, by Reaction 1:
  • reaction product was cooled to room temperature and passed through a Celite pad using dichloromethane, and solvents were removed by distillation under reduced pressure.
  • reaction product was cooled to room temperature, and 100 mL of distilled water was added thereto, followed by stirring at room temperature for about one hour.
  • the solid thus precipitated was filtered under reduced pressure using distilled water and methanol to obtain a gray solid.
  • a slurry process e.g., rinsing and/or recrystallization
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 3.1 g (yield: 88.4%) of Compound 4 as a yellow solid.
  • the molecular weight of Compound 4 measured by FAB-MS was 450. Through the results, the compound thus obtained was identified as Compound 4.
  • Polycyclic Compound 5 according to an embodiment may be synthesized, for example, by Reaction 2:
  • the solid thus precipitated was filtered using distilled water and methanol to obtain a gray solid.
  • a slurry process e.g., rinsing and/or recrystallization
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 2.5 g (yield: 76.4%) of Compound 5 as a yellow solid.
  • the molecular weight of Compound 5 measured by FAB-MS was 451. Through the results, the compound thus obtained was identified as Compound 5.
  • Polycyclic Compound 6 according to an embodiment may be synthesized, for example, by Reaction 3:
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 2.3 g (yield: 70.2%) of Compound 6 as a yellow solid.
  • the molecular weight of Compound 6 measured by FAB-MS was 475. Through the results, the compound thus obtained was identified as Compound 6.
  • Polycyclic Compound 10 according to an embodiment may be synthesized, for example, by Reaction 4:
  • Polycyclic Compound 11 according to an embodiment may be synthesized, for example, by Reaction 5:
  • the solid thus precipitated was filtered using distilled water and methanol to obtain a gray solid.
  • a slurry process e.g., rinsing and/or recrystallization
  • Polycyclic Compound 38 according to an embodiment may be synthesized, for example, by Reaction 6:
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 0.74 g (yield: 18.3%) of Compound 38 as a yellow solid.
  • the molecular weight of Compound 38 measured by FAB-MS was 581. Through the results, the compound thus obtained was identified as Compound 38.
  • Polycyclic Compound 72 according to an embodiment may be synthesized, for example, by Reaction 7:
  • reaction product was cooled to room temperature and 100 mL of distilled water was added thereto, followed by stirring at room temperature for about one hour.
  • the solid thus precipitated was filtered using distilled water and methanol to obtain a gray solid.
  • a slurry process (e.g., rinsing and/or recrystallization) was performed for the solid thus obtained using dichloromethane and methanol to obtain 2.85 g (yield: 60.8%) of an ivory solid compound, Intermediate (12).
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 2.21 g (yield: 50.1%) of Compound 72 as a yellow solid.
  • the molecular weight of Compound 72 measured by FAB-MS was 631. Through the results, the compound thus obtained was identified as Compound 72.
  • Polycyclic Compound 77 may be synthesized, for example, by Reaction 8:
  • reaction product was cooled to room temperature and 100 mL of distilled water was added thereto, followed by stirring at room temperature for about one hour.
  • the solid thus precipitated was filtered under reduced pressure using distilled water and methanol to obtain a gray solid.
  • a slurry process (e.g., rinsing and/or recrystallization) was performed for the solid thus obtained using dichloromethane and methanol to obtain 3.88 g (yield: 67.2%) of an ivory solid compound, Intermediate (13).
  • a slurry process (e.g., rinsing and/or recrystallization) was performed using dichloromethane and methanol to obtain 2.8 g (yield: 51.4%) of Compound 77 as a yellow solid.
  • the molecular weight of Compound 77 measured by FAB-MS was 782. Through the results, the compound thus obtained was identified as Compound 77.
  • Table 1 shows the lowest singlet excitation energy level (S1 level), the lowest triplet excitation energy level (T1 level), and the ⁇ E ST of each of Compound 4, Compound 5, Compound 6, Compound 10, Compound 11, Compound 38, Compound 72, Compound 77, Comparative Compound C1, and Comparative Compound C2.
  • the energy level values in Table 1 were calculated by a nonempirical molecular orbital method, e.g., using a B3LYP/6-31G(d) hybrid density functional and basis set using Gaussian 09 of Gaussian Co.
  • ⁇ E ST refers to the difference between the lowest singlet excitation energy level (S1 level) and the lowest triplet excitation energy level (T1 level).
  • Organic electroluminescence devices including the polycyclic compound of an embodiment in an emission layer were manufactured according to the method below.
  • the organic electroluminescence devices of Example 1 to Example 8 were manufactured using the polycyclic compounds of Compound 4, Compound 5, Compound 6, Compound 10, Compound 11, Compound 38, Compound 72, and Compound 77, respectively, as the dopant materials of an emission layer.
  • Comparative Example 1 and Comparative Example 2 were manufactured using Compound C1 and Compound C2, respectively, as the emission layer dopant materials.
  • a glass substrate including a patterned ITO layer was washed using ultrapure water and ultrasonic waves, exposed to ultraviolet light for about 30 minutes, and treated with ozone. Then, HT1 was deposited to a thickness of about 1,200 ⁇ , and HT2 was deposited to a thickness of about 100 ⁇ to form a hole transport region.
  • the compound of an embodiment or a Comparative Compound was co-deposited with mCBP in a ratio of about 20:80 to a thickness of about 400 ⁇ to thereby form an emission layer.
  • the emission layer co-deposited was formed by mixing and depositing each compound of the present disclosure with mCBP in the Examples, and by mixing and depositing the Comparative Compounds with mCBP in the Comparative Examples.
  • ET and LiQ were mixed and deposited in a ratio of about 5:5 on the emission layer to form a layer having a thickness of about 300 ⁇ , and a layer was formed using LiQ to a thickness of about 10 ⁇ to form an electron transport region.
  • a second electrode was formed using Mg:Ag (10:1) to a thickness of about 100 ⁇ .
  • the hole transport region, the emission layer, the electron transport region, and the second electrode were formed using a vacuum deposition apparatus.
  • the devices achieved relatively high emission efficiency and external quantum efficiency compared with the devices of the Comparative Examples.
  • the Example Compounds exhibit TADF properties because they have multiple resonance phenomenon due to the polycyclic aromatic ring, include indolophenazine or indolophenoxazine moiety as an electron donor, and have a structure in which an electron donor and an electron acceptor are connected via a linker, such that a small ⁇ E ST value may be achieved when compared with Comparative Compounds C1 and C2.
  • the organic electroluminescence devices of the Examples may show improved emission efficiency than the organic electroluminescence devices of the Comparative Examples.
  • the organic electroluminescence device of an embodiment includes the polycyclic compound of an embodiment as a material for an emission layer, high emission efficiency could be achieved in a red light or green light wavelength region.
  • the organic electroluminescence device of an embodiment may show improved device properties showing high emission efficiency in a blue region.
  • the polycyclic compound of an embodiment may be included in the emission layer of an organic electroluminescence device, and may contribute to the high efficiency of the organic electroluminescence device.
  • any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range.
  • a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6.
  • Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070241670A1 (en) * 2006-04-17 2007-10-18 Battelle Memorial Institute Organic materials with phosphine sulfide moieties having tunable electric and electroluminescent properties
US20080114924A1 (en) * 2006-11-13 2008-05-15 Jack Edward Frayer High bandwidth distributed computing solid state memory storage system
WO2012077582A1 (en) * 2010-12-10 2012-06-14 Canon Kabushiki Kaisha Indolophenoxazine compound and organic light emitting device using the same
KR101305934B1 (ko) 2010-11-19 2013-09-12 한국과학기술연구원 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20150130797A (ko) 2014-05-14 2015-11-24 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
US20170069849A1 (en) * 2015-09-08 2017-03-09 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US20170077420A1 (en) * 2015-08-25 2017-03-16 Arizona Board Of Regents On Behalf Of Arizona State University Thermally Activated Delayed Fluorescent Material Based on 9,10-Dihydro-9,9-dimethylacridine Analogues for Prolonging Device Longevity
KR20170111387A (ko) 2016-03-28 2017-10-12 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070241670A1 (en) * 2006-04-17 2007-10-18 Battelle Memorial Institute Organic materials with phosphine sulfide moieties having tunable electric and electroluminescent properties
US20080114924A1 (en) * 2006-11-13 2008-05-15 Jack Edward Frayer High bandwidth distributed computing solid state memory storage system
KR101305934B1 (ko) 2010-11-19 2013-09-12 한국과학기술연구원 화합물 및 이를 이용한 유기전기소자, 그 단말
WO2012077582A1 (en) * 2010-12-10 2012-06-14 Canon Kabushiki Kaisha Indolophenoxazine compound and organic light emitting device using the same
KR20150130797A (ko) 2014-05-14 2015-11-24 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
US20170077420A1 (en) * 2015-08-25 2017-03-16 Arizona Board Of Regents On Behalf Of Arizona State University Thermally Activated Delayed Fluorescent Material Based on 9,10-Dihydro-9,9-dimethylacridine Analogues for Prolonging Device Longevity
US10211411B2 (en) 2015-08-25 2019-02-19 Arizona Board Of Regents On Behalf Of Arizona State University Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity
US20170069849A1 (en) * 2015-09-08 2017-03-09 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
KR20170030130A (ko) 2015-09-08 2017-03-17 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자
KR20170111387A (ko) 2016-03-28 2017-10-12 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

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